| Summary: | We disclose a novel synthetic method to access the homocubane ester 4a in 4 steps, in an overall yield comparable or superior to literature methods. The sequential transformations of a [6+2] cycloaddition, 4π electrocyclisation, followed by a dehydrogenation and [2+2] cycloaddition displays the relatively simple route to access this challenging to make structure. We also inadvertently synthesised an interesting polycyclic structure we have tentatively assigned as formal [4+2] product 6.
Herein, we report the development of a methodology for the regioselective 1,4-addition of propargyl boronates to a range of N-alkylated pyridinium, quinolinium, and pyrazinium salts, through gold-(I) mediated catalysis. A variety of functionality is tolerated under the mild reaction conditions, and an attempt to rationalise the mechanism has been realised with the assistance of DFT studies. Further potential chemical transformations have also been conducted, which, when combined with the work conducted in this study, pave the way for exploration into underdeveloped and diverse chemical space.
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